Hydrochloric Acid → 2-(Methyl-3-nitro-benzyl)-isoindole-1,3-dione

HRID 1454288Notes

Reaction equation

HRID 1454288 reaction equation
C[C:2]1[CH:13]=[CH:12][C:5]([CH2:6]OS(C)(=O)=O)=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].[CH3:17]N(C=O)C.[C:22]1(=[O:32])[NH:26][C:25](=[O:27])[C:24]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:23]12.[K].Cl>CCCCCC.C(OCC)(=O)C>[CH3:17][CH:6]([N:26]1[C:22](=[O:32])[C:23]2[C:24](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:25]1=[O:27])[C:5]1[CH:12]=[CH:13][CH:2]=[C:3]([N+:14]([O-:16])=[O:15])[CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 208002884-Methyl-3-nitrobenzyl methanesulfonateHCID 24194345Phthalimide potassium salt

Product 1

HCID 223935242-(Methyl-3-nitro-benzyl)-isoindole-1,3-dione

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Methanesulfonic acid 4-methyl-3-nitro-benzyl ester (0.45 g, 1.83 mmol) was added to anhydrous DMF (20 mL), under argon, and potassium phthalimide (0.34 g, 1.83 mmol) was added. The reaction mixture was heated to 60EC for 12 h. The reaction mixture was cooled and poured into 1N HCl and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with water, brine and dried over anhydrous magnesium sulfate. The solution was filtered and the solvent removed under reduced pressure. The product was isolated by flash chromatography. (4:1 hexane/ethyl acetate) Yield 0.45 g. 1H NMR (CDCl3, 300 MHz): δ 2.58 (s, 3H), 4.88 (s, 2H), 7.30 (d, J=7 Hz, 1H), 7.57 (d, J=7 Hz, 1H), 7.24-7.77 (m, 2H), 7.84-7.89 (m, 2H), 8.02 (s, 1H).

Workup

  1. temperatureThe reaction mixture was heated to 60EC for 12 h
  2. temperatureThe reaction mixture was cooled
  3. extractionthe aqueous layer was extracted three times with ethyl acetate
  4. washThe combined organic layers were washed with water, brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe solution was filtered
  7. customthe solvent removed under reduced pressure
  8. customThe product was isolated by flash chromatography

Sources & evidence

ORD record
ord-a802a2e2bf08422f94821e94216eb39c
Source dataset
uspto-grants-2009_01
Patent number
US07479495B2

Reaction notes

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